2-(4-Cyanophenoxy)acetic acid → HCID 18412580, compound

HRID 50200Notes

Reaction equation

HRID 50200 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9](O)=O)=[CH:5][CH:4]=1)#[N:2].[NH2:14][C:15]1[C:20]([NH:21][CH3:22])=[CH:19][CH:18]=[C:17]([CH3:23])[N:16]=1>O1CCCC1>[CH3:22][N:21]1[C:20]2[C:15](=[N:16][C:17]([CH3:23])=[CH:18][CH:19]=2)[N:14]=[C:9]1[CH2:8][O:7][C:6]1[CH:12]=[CH:13][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 7360972-(4-Cyanophenoxy)acetic acidHCID 18412465HCID 18412465, compound

Product 1

HCID 18412580HCID 18412580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.4 g (63 mmol) of 4-cyanophenoxyacetic acid were dissolved in 200 mL of absolute tetrahydrofuran and mixed at room temperature with 10.2 g (63 mmol) of N,N′-carbonyldiimidazole. After 15 minutes at 60° C., 5.70 g (41.5 mmol) of 2-amino-3-methylamino-6-methylpyridine were added. After 2 hours at 60° C., the solvent was distilled off and the crystalline residue was mixed with water, washed with water, and dried. After crystallization from ethanol, 9.95 g (91% of theory) were obtained in the form of white crystals. C16H14N4O (278.32). Mass spectrum: M+=278.

Workup

  1. waitAfter 2 hours at 60° C.
  2. distillationthe solvent was distilled off
  3. additionthe crystalline residue was mixed with water
  4. washwashed with water
  5. customdried
  6. customAfter crystallization from ethanol
  7. custom9.95 g (91% of theory) were obtained in the form of white crystals

Sources & evidence

ORD record
ord-155db5bb947b455ebd5997a0332e3da3
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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